1976: Kenneth Dart graduated from the University of Michigan with a degree in mechanical engineering.
1986: He joined the family business and became president of the Dart Container Corporation.
1994: Dart became a citizen of Belize. At that time Dart offered his residence in Sarasota, Florida, to the government of Belize as a consulate with himself as its consul. This would have allowed him to live in the United States full-time as a foreign diplomat avoiding any actions by the Internal Revenue Service; the State Department rejected the arrangement.
1996: A tightening of U.S. tax laws concerning expatriates, was partially spurred by the Dart brothers' renunciation of their citizenship to avoid paying taxes. Kenneth took Caymanian, Belizean and, later, Irish, citizenship. Kenneth Dart acquired citizenship of, and a compound in, the Cayman Islands. He owns a number of Cayman-based enterprises, including Dart Enterprises, Dart Realty, and Cayman Shores Development. His Caymanian enterprises are estimated to own about 20–25% of the real estate in the Cayman Islands.
2001: His brother Robert succeeded him in this role, when Kenneth moved to the board of directors.